shoes with dresses in winter What to Wear Skirts and — Inside Out Style 10 Fall Shoes To Wear

I love how this style offers warmth without the bulk- you get the benefit of the overlapping front, which adds an extra layer at the chest to keep you cozy

MORE: Vintage shoe stores: See what shoe shopping really used to be like Chunky shoes, all lopped off at the toe for the square look, are being shown in earthy colors like mushroom and goldenrod. Hardware gets its biggest play here

Id avoid loafers with heavy stitching, embellishments, or chunky soles since those can make the look feel bulky against wide leg pants

Lauren Sanchez, 2025 (L-R) Lauren Sanchez and Jeff Bezos attend the F1 Grand Prix of Monaco on May 25, 2025 in Monte-Carlo, Monaco

On sale for $61.20

100% cotton, french cuffs, Black gold trimmed buttons, hidden button down collar